1. Field of Invention
The present invention relates to a hydrogenation process of chloronitrobenzene. More particularly, the present invention relates to a hydrogenation process of chloronitrobenzene with the use of nanosized boron-containing nickel catalyst.
2. Description of Related Art
Conventionally, the noble metal is used as the catalyst in the liquid-phase hydrogenation process of chloronitrobenzene, wherein the catalyst includes palladium (Pd), platinum (Pt) and ruthenium (Ru). That is, by using the noble metal as the catalyst, the ortho-chloronitrobenzene is hydrogenated into the ortho-chloroaniline, the meta-chloronitrobenzene is hydrogenated into the meta-chloroaniline and the para-chloronitrobenzene is hydrogenated into the para-chloroaniline.
In the Journal of Applied Catalysis (vol. 76, pages 255-266, 1991), Figueras et al. disclose the use of the ruthenium as the reaction catalyst in the hydrogenation process of the ortho-chloronitrobenzene. In addition, Liao et al., in J. Chem. Soc., Chem. Comm. (pages 1155-1156, 1995), described the use of palladium-ruthenium bi-metals as the reaction catalyst in the hydrogenation process of the ortho-chloronitrobenzene. Furthermore, Liu et al., in Applied Catalysis A: General (vol. 164, pages 197-203, 1997), disclosed the use of platinum cluster as the reaction catalyst in the hydrogenation process of the para-chloronitrobenzene. Moreover, in Catalysis Letter (vol. 44, pages 205-210, 1997), Vitulli et al. revealed the use of platinum/aluminum oxide as the reaction catalyst in the hydrogenation process of the ortho-chloronitrobenzene. Also, Liu et al. in J. Molecular Catalysis A: Chemical (vol. 147, pages 55-62, 1999) disclosed the use of palladium-platinum bi-metals as the reaction catalyst in the hydrogenation process of the para-chloronitrobenzene. Further, Liu et al. in J. Molecular Catalysis A: Chemical (vol. 159, pages 115-120, 2000) illustrated the use of platinum mixed with the polyvinyl alcohol surfactant as the reaction catalyst in the hydrogenation process of the ortho-chloronitrobenzene. Liu et al. in J. Molecular Catalysis A: Chemical (vol. 170, pages 203-208, 2001) revealed the use of ruthenium mixed with the polyvinyl alcohol surfactant as the reaction catalyst in the hydrogenation process of the para-chloronitrobenzene.
In addition, in American Patent with the U.S. Pat. No. 4,326,078, the noble metal is used as the reaction catalyst for hydrogenating nitrobenzene to form oxy-azobenzene. Further, American Patent with the U.S. Pat. No. 4,140,719 disclosed the use of the phase-shifting catalyst for fluorinating the 2,4,5-trichloro nitrobenzene to form 2,4-difluoro nitro benzene.
However, the conventional hydrogenation processes mentioned in all the documents and the issued patterns use noble metal such as palladium, platinum and ruthenium as the reaction catalyst. The noble metal is expensive and possesses high hydrogenation ability. Therefore, it is easy to generate byproducts during the hydrogenation process.